(R,E)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoate

Product Name: (R,E)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoate
CAS No.: 149709-59-1
Chemical Name: (R,E)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoate
Synonyms: LCZ696 59-1;LCZ-696-003-R;Sacubitril Impurity 107;LCZ696(valsartan + sacubitril) impurity 24;Valsartan Impurity14(mixture of E/Z-isomers);(R,E)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl...;(R)-Ethyl 5-(biphenyl-4-yl)-4-(tert-butoxycarbonylamin)-2-methylpent-2-enoate;(R)-Ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpent-2-enoate;(R,E)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoate;Ethyl 5-(4-[1,1'-biphenyl]yl)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methyl-2-pentenoate
CBNumber: CB02723686
Molecular Formula: C25H31NO4
Formula Weight: 409.52
MOL File: 149709-59-1.mol

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(R,E)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoate Property

Boiling point:: 562.7±50.0 °C(Predicted)
Density: 1.081±0.06 g/cm3(Predicted)
storage temp.: 2-8°C
pka: 11.14±0.46(Predicted)
Appearance: Off-white to light yellow Solid
optical activity: -31.5534°(C=0.5665g/100ml CHCL3)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC

Product number: E901513
Product name: (R)-Ethyl5-([1,1''-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpent-2-enoate
Packaging: 1g
Price: $130
Updated: 2021/12/16

TRC

Product number: E901513
Product name: (R)-Ethyl5-([1,1''-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpent-2-enoate
Packaging: 100mg
Price: $90
Updated: 2021/12/16

Matrix Scientific

Product number: 167900
Product name: (R,E)-Ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoate
Packaging: 10g
Price: $1486
Updated: 2021/12/16

Ambeed

Product number: A237269
Product name: (R)-Ethyl5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpent-2-enoate
Purity: 97%
Packaging: 5g
Price: $92
Updated: 2021/12/16

Chemenu

Product number: CM249639
Product name: (R)-Ethyl5-([1,1''-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpent-2-enoate
Purity: 95+%
Packaging: 5g
Price: $122
Updated: 2021/12/16

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(R,E)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoate Chemical Properties,Usage,Production

Uses

(R)-Ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpent-2-enoate is used to prepare dicarboxylic acid dipeptide neutral endopeptidase inhibitors.

Synthesis

149818-98-4

21382-82-1

149709-59-1

Step 5: 23.3 g of the product of Step 4 ((R,E)-ethyl 5-([1,1'-biphenylyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpent-2-enoate, 65.6 mmol, 1.0 eq.) was dissolved in 300 mL of dichloromethane (DCM) and cooled under a nitrogen (N2) atmosphere to -70° C. At this temperature, dropwise 109 mL of diisobutylaluminum hydride (DIBAL-H, 1.5 M toluene solution, 164 mmol, 2.5 eq.) was added. After stirring for 15 minutes, thin layer chromatography (TLC) analysis showed that there was still raw material residue. Subsequently, an additional 15 mL of DIBAL-H (1.5 M toluene solution) was added dropwise and stirring was continued for 5 minutes at -70°C. TLC showed that the reaction was complete. The reaction solution was slowly poured into 450 mL of 1 M aqueous hydrochloric acid (HCl), keeping the temperature below 0°C. After stirring for a few minutes, the organic layer was separated and the aqueous phase was extracted with DCM (100 mL × 2). The combined organic layers were washed sequentially with aqueous sodium bicarbonate (NaHCO3) (150 mL) and water (100 mL) and dried over anhydrous sodium sulfate (Na2SO4). After filtration, 19.0 g of ethyl 2-(triphenylphosphoranylidene)propionate was added to the solution, keeping the temperature below 5°C. The resulting solution was stirred at 25°C for 18 h. TLC showed that the reaction was complete. The reaction solution was concentrated, purified by silica gel column chromatography (petroleum ether/ethyl acetate = 4/1) and then crystallized from petroleum ether/ethyl acetate (80 mL/20 mL) to afford 17.0 g of ethyl (4R)-5-[1,1'-biphenyl]-4-yl-4-[[tert-butoxycarbonyl]amino]-2-methyl-2-pentenoate (chemical purity > 99.5%) as a white solid. Total yield in two steps: 89.1%.

References

[1] Patent: WO2015/154673, 2015, A1. Location in patent: Page/Page column 16

(R,E)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoate Preparation Products And Raw materials

Raw materials

Preparation Products

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(R,E)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoate Suppliers

China 92 India 2 United States 4 Global 98

Pharmaffiliates Analytics and Synthetics P. Ltd

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Email: mktg@pharmaffiliates.com
Country: India
ProdList: 6739
Advantage: 58

A.J Chemicals

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View Lastest Price from (R,E)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoate manufacturers

Career Henan Chemical Co

Product: (R,E)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoate 149709-59-1
Price: US $100.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 100KG
Release date: 2018-07-27

149709-59-1, (R,E)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoateRelated Search:

(2S,4S)-5-(Biphenyl-4-yl)-4-[(tert-butoxycarbonyl)amino]-2-methylpentanoic acid (R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid LCZ Impurity (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoic acid hydrochloride AHU-377 (S)-5-[(Biphenyl-4-yl)carbonyl]pyrrolidin-2-one LCZ696 InteMediate (2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoate (2S,4R)-5-(Biphenyl-4-yl)-4-[(tert-butoxycarbonyl)amino]-2-methylpentanoic acid sacubitril (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoic acid (2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-aMino-2-Methylpentanoate AHU-377 (heMicalciuM salt) Valsartan (2R,4R)-5-(Biphenyl-4-yl)-4-[(tert-butoxycarbonyl)amino]-2-methylpentanoic acid Ethyl (2R,4S)-4-([1,1'-biphenyl]-4-ylmethyl)-2-methyl-4-(2,5-dioxopyrrolidin-1-yl)butanoate (2R,4S)-4-([1,1'-Biphenyl]-4-ylmethyl)-4-(4-ethoxy-4-oxobutanamido)-2-methylbutanoic acid N-[2’-(1H-tetrazol-5-yl)biphenyl-4-yl methyl]-N-Valeryl-(L)-Valine benzyl ester

(R,E)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoate

(4R)-5-[1,1'-Biphenyl]-4-yl-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methyl-2-pentenoic acid ethyl ester

2-Pentenoic acid, 5-[1,1'-biphenyl]-4-yl-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methyl-, ethyl ester, (4R)-

Ethyl 5-(4-[1,1'-biphenyl]yl)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methyl-2-pentenoate

LCZ696 59-1

(R)-Ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpent-2-enoate

LCZ-696-003-R

LCZ696(valsartan + sacubitril) impurity 24

(R,E)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl...

Valsartan Impurity14(mixture of E/Z-isomers)

C25H31NO4 (R,E)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoate 149709-59-1

Sacubitril Impurity 107

(R)-Ethyl 5-(biphenyl-4-yl)-4-(tert-butoxycarbonylamin)-2-methylpent-2-enoate

149709-59-1

LCZ696